


Short and Saucy Kim Possible Character Studies

by EdgarNeeley



Category: Kim Possible (Cartoon)
Genre: F/M
Language: English
Status: In-Progress
Published: 2019-08-19
Updated: 2020-03-25
Packaged: 2020-09-07 21:14:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 29
Words: 13,225
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20316118
Author URL: https://archiveofourown.org/users/EdgarNeeley/pseuds/EdgarNeeley
Summary: Some lewd character drabbles for various Kim Possible characters, now with some branching into longer connected stories. Use the comments to tell me which one you liked the most or which one you want to see a follow up to.





	1. Ann

Ann's husband was always a bit of a space cadet, his mind sometimes seemed to be a thousand miles away and yet when she'd married him it was something she'd found endearing. Now though after 3 kids his inattentiveness was becoming unbearable even on the nights when he wasn't working late at the space center. A woman could only reach for her vibrator so many times before she began to question her situation.

At the same time her daughter's best friend was growing into a handsome young man and he always seemed to have time to talk with her, laugh at her jokes or give her a hand with the chores. He was a fine catch if Kim ever opened her eyes and realized it, and Ron was certainly around the house a lot more than James was so it wasn't unreasonable that Ann began to think about him.

It started when some of his innocent compliments took on a different, more risqué meaning in her own mind. She started having these waking dreams; spacing out while she watched him chow down on a snack she'd made for him and thinking of how he might return the favor by bending her over the counter and giving her pussy a taste of that nice hard cock that she knew would be so full of youthful energy and stamina.

She assumed these thoughts would only be a passing fancy but the dreams continued and became more torrid, her imaginary love affair growing day by day. Left unfulfilled her fantasies grew so debauched that even her own daughter gained a supporting role in some of them. She knew that she was a bad wife for lusting after another man, much less one young enough to be her son, but that didn't stop her from imagining it was him every time she used a toy in place of her absent husband.

Hearing the backdoor open and the telltale sound of Ron's sneakers on the linoleum she felt her panties grow wet in response and wondered if today would be the day she gave in and tried to make her fantasies a reality.


	2. Bonnie

Bonnie was a popular girl at school, though really that should be a given. She was stunningly attractive, she was friends with all the right people, and she had a body the boys drooled over. And it wasn't like she had any problems with the attention, she loved it and she loved the way it boosted her to the top of the social ladder. She was a queen.

Fittingly her first boyfriend in high school was the captain of one of the sports teams, the lacrosse team. After all why should she settle for less when guys were throwing themselves at her? He was popular and hunky and it didn't take long before he wanted to go all the way with her. Of course once isn't enough for any guy but Bonnie found she was more than happy to start spending their dates in the backseat of his car.

After she broke up with him she had more boyfriends, more team captains befitting her social status, but she liked to keep herself open even when she was dating. It would be stupid not to when there were so many hot guys willing to give her what she craved and all she had to do was ask. People started to whisper when it became common knowledge that she often slept with more than one in the same night. They thought she couldn't hear what they were calling her behind her back, but she did: "Slut."

But she didn't take it as an insult. Let them call her a slut if that's what you called a girl who got what she wanted. And her new title removed barriers she hadn't even noticed before. Now at parties she didn't need to take a guy upstairs, instead she'd ride his dick in full view of everyone. If they were celebrating a win she'd run a train with the whole team, making sure each one of them finished on her face while everyone chanted her name. She was the best girl and the center of attention. She was the queen of the sluts.


	3. Yori

Yori was a skilled ninja, raised by and loyal to the Yamanouchi School. She had spent her life learning the arts and that was why Master Sensei had entrusted her with this most sensitive task. After centuries of waiting the Mystical Monkey Power had reemerged in a young man and it was up to her to bring him to the school where that power would one day be needed.

She had been told he was an American and braced herself for the worst. But Ron Stoppable was surprisingly sweet and kind, a gentle soul who she could not deny was very pleasing to her eyes as well. It made her want to tell him of the importance of his powers and the connection to her school's founder Toshimiru, but she couldn't do that until after he had been convinced to stay.

Becoming his friend was natural but it wasn't enough to make him give up his old life. Appealing to baser urges failed too, not because his heart was made of stone, but because he seemed innocently oblivious to the lewd hints and offerings she kept making to him. Seeing what a good man he was strained her resolve to continue deceiving him but too much was at stake, she had to take drastic action.

It was good that Ron had never tasted sake before and didn't know it was alcohol. Once he'd had enough she slid off her kimono and experienced great joy at his now uninhibited reaction. Letting him lead her as much as she led him they indulged many forbidden desires and she hoped he would stay not just for the school's sake but for her own, so they could repeat this coupling every night. However she had perhaps given him too much and by the morning he remembered nothing.

Yori was sad to see her Stoppable-san go but when she approached Master Sensei he still congratulated her on her success. As the test would confirm there would be a new master of Mystical Monkey Power born right there at the Yamanouchi School.


	4. Shego

Shego was once a hero. Along with her brothers they were Team Go and they defended the city from villains. It wasn't a bad gig and she would've probably kept it if it wasn't for the fans.

She couldn't stand her fans, they were all men and to her they were all disgusting. She had nearly charbroiled a few of them. But the reason she had to leave was actually because of her brother's fans, the girls. She lusted over them, wanted to do all kinds of unspeakable things to them. If those deviant ideas ever got out then Team Go would have been ruined.

So she'd left and became a villain. It wasn't a bad gig and for a while things went smoothly again. And then Kim Possible appeared on the scene. The first time they met she blew the fight because she was so distracted by this hot little teen in her sexy midriff flaunting outfit. The way Kim made her body bend and flex while she fought made Shego think she was watching the intro to her ideal porno. Shego wanted her.

But she didn't want her as a girlfriend. She knew that she wanted to defeat Kim fair and square and then chain her up in a dungeon. She'd light up a fingertip with green flame and steadily deconstruct that enticing hero ensemble one piece at a time to get at the nubile girl underneath. And with her biggest strap-on she'd plow that virgin ass until she'd extracted every single scream that Kim Possible had to give.

Once she was broken Shego would put her back together and rename her Princess. Those tiny tits would get shiny gold piercings joined by a permanent chain that Shego could yank on whenever she pleased. Above the girl's clit she'd tattoo her name along with "Property of" so it would be clear to everyone when she passed Princess around at some of the more extreme underground clubs she knew about.

For Kim it was fortunate that Shego was still throwing their fights, wary of her own actions if she ever won.


	5. Ron

Ron was the only guy on the Middleton Cheerleading squad. As the mascot he didn't wear a skirt or a skimpy tit hugging top. And being the only guy he had to find somewhere else to change and was often excluded from other activities, at least until Kim put her foot down. It was cheer camp and Bonnie had brought a game of dare cards with some smuggled in booze. Kim made it clear that unless Ron could join too she'd end the after dark mischief.

But she might not have picked that as her battle if she knew what was on those cards. Bonnie had brought a very lewd deck and Ron became the only available target for many of the more shocking dares the girls had to do. The game let them become very intimately acquainted with their only male team member and eventually they all watched each other ride him to orgasm.

But he never once bragged about how he'd scored with every cheerleader in the same night and that won him a lot of respect for his discretion, in addition to what he'd already gotten for his stamina. It also let him earn 'mascot privileges'.

Being on trips away from their boyfriends or even just too busy with extracurriculars to have one left a lot of horny cheerleaders. They agreed to offer Ron the chance to have sex with them anytime he wanted as long as the arrangement went both ways and they could tell him when they needed some Ronshine, from a pussy licking to a deep dicking.

Now he got changed in the girl's locker room, showering off the sweat he got inside the costume while enjoying a stunning view of 8 lovely ladies rubbing their naked bodies under the spray. Getting a hard-on he didn't need to be embarrassed, he only needed to pick the girl he wanted and step up behind her. Cooing she'd say his name and widen her legs so he could start fucking her right there against the wall. It was good to be the Mad Dog.


	6. Monique

Monique was a fashion icon even though she was just a student in her senior year. Her weekly live stream in which she talked shop about fashion and modeled some of her latest creations often boasted thousands of viewers.

How a high school girl could gain such an enormous following wasn't clear unless you really sat down and watched it yourself. At first it was obvious that some of her designs were a bit risqué, finding creative and alluring bits of skin to show off, and maybe that brought in a few extra viewers. But it still seemed like it was mostly about an admittedly attractive black girl in her bedroom talking about the best stitches and seam styles.

The secret wouldn't be revealed until it was time to switch outfits. In the beginning she went just off camera to do it, so occasionally a leg or an elbow or maybe something more interesting would be caught on screen. Soon a small mirror happened to be installed on the back wall and those in the know could zoom in to catch a lot more. Finally Monique dropped the pretense about what she wanted people to see and started changing right on camera without missing a beat.

Now her fans tuned in each week to see her naked ass shimmying into a sparkling vinyl mini-dress or watch her squeeze those delicious chocolate boobs together in between her hands so that they could be fit into her latest creation. Prior to Monique's Fashion Hour it's unlikely that anyone realized how many lewd sewing based puns could be made. She always smiled and winked at the camera knowing that everyone was enjoying the show.

The only real concern was keeping out anyone who would endanger her channel by making it obvious how not truly innocent it was. Asking for tits got you banned from chat instantly; she just couldn't let anyone ruin this for her. She wanted everyone to see her hot inspired designs and just as equally wanted everyone to see her hot naked body.


	7. Kyoko

Kyoko was the personal assistant to Mr. Nakasumi, head of the mighty Nakasumi Toys. She had many duties including acting as his translator when he pretended to not speak English. One duty not known to westerners but common in her country was that of a female facilitator. For big ventures she would sit by Mr. Nakasumi as he talked to a potential business partner over a traditional meal, after which she would be told to accompany that man up to his hotel room and 'help' him come to a decision.

Outsiders would call the practice demeaning, objectifying women and trading them like currency. But Kyoko liked doing it, these older men thought they were so powerful but it was easy to wrap them around her finger. She'd make those sharp cries they all loved as she bounced her nimble body on their lap and enjoyed their dicks stirring up her insides. Lost in their lustful state she frequently coaxed them into paying double what Mr. Nakasumi had originally asked for.

But her most enjoyable assignment was of a very different sort. Team Possible had saved Mr. Nakasumi and his company twice, but Kim Possible (perhaps not understanding the importance of the custom) steadily refused to accept any reward beyond a ride home. However her partner Ron had remained silent and Mr. Nakasumi told her to take him to the back of the plane and ensure that he received a gift that matched the rank and importance of the man he had saved.

In the jet's private bedroom suite she was not surprised to learn that Ron had limited experience with girls. It was thrilling to show him new things, like how deep his dick could really go inside a girl's mouth. When they joined together it was with her on her back so that she could tell him to fuck her as hard as he wanted and she wasn't disappointed with the results. When they returned to the cabin she gave him a quick kiss on the cheek and told him she looked forward to the next time he came to Mr. Nakasumi's rescue.


	8. Zita

Zita was something of an internet connoisseur. There was an art to finding, bookmarking and organizing all the best links. Every day she'd pour over a list of sites looking for juicy new submissions. Of course what she was looking for was porn. Apart from playing games watching porn was the main thing she did with the computer she spent so many hours. She was maybe a bit of a porn addict.

But that wasn't wrong she argued. Sure she could look for a real boyfriend, but could any guy give her as much variety as her computer screen did? Right now she could be masturbating to a wild lesbian orgy filled with strap-ons and squirting, then immediately be going for another orgasm watching as a sexy 'stepmom' seduced a hot looking guy she was calling son before finally capping the night off with a muscle bound hunk on top pumping into an even more muscle bound hunk below.

She did eventually meet a guy she liked. Ron was funny and they managed to go on a few good dates. But eventually she just wanted to stay in and so they sat side by side on her coach watching a porno with 6 big black guys all ganging up on this absolutely tiny little white girl. It did feel good having Ron finger her while she jacked him off but in the end it wouldn't be that different doing it herself and then she wouldn't have to deal with all the other stuff a relationship entailed, she could just go straight to the porn.

So she went back to browsing the web alone. There was still so much to find and she got into things like bondage and watersports and even found some sites that she wasn't even sure were legal in her country. In her room with her headphones on she worked every night making a puddle under her chair as she gave herself an orgasm marathon that only unlimited access to porn could provide.

**Notes for the Chapter:**

> Did this one end a little too dark? I didn't mean it to.


	9. Kim

Kim was best friends with Ron since pre-k. They'd done everything together from school projects, to cheer squad, to saving the world. After prom where they finally became more than just friends their sensual consummation was free of any of the awkwardness that other couples usually endured. Already together for so much Kim and Ron felt 100% comfortable with each other.

So when Ron admitted to an interest in a Japanese exchange student Kim felt no jealousy and immediately arranged a ride to Japan. Yori was surprisingly quick to agree and Kim watched as her boyfriend lewdly indulged himself with the Asian girl's body before she gave him a tantalizing show by having sex with Yori herself. Before leaving they found many ways for the three of them to give each other pleasure simultaneously.

And while missions were usually already stressful enough for him Ron didn't turn down the extra burden when Kim said she wanted to spice things up for herself. Shego was probably confused out of her mind as to why Kim was enjoying their fight far too much to make any sense. With Ron carefully operating the remote even as he raced Dr. Drakken to the controls of his doomsday machine the little egg made Kim scream in ecstasy with every flip and dodge she made and with every punch or kick she landed.

And sometimes their wishes overlapped serendipitously, like when Kim wanted to see how much farther Ron's stamina would go with some blue pills and he wanted to try out Kim's ass. It was smart that they'd used a fake mission as the cover for their absence because by morning Kim could only stand or lay on her side though she didn't regret at all how she'd brought on her own ass wrecking.

Being known as a world saving team became invaluable in concealing and supporting the needs of their growing sexual experimentation. It soon became clear that absolutely nothing was too kinky for one of them to ask the other one to try.


	10. Tara

Tara was a sweat bubbly girl, the typical pretty blonde everyone was friends with. Everything should be going right for her but Tara's relationships kept fizzling out because she couldn't tell her boyfriends what she really wanted in the bedroom.

After watching certain Hollywood movies she'd developed an embarrassing desire to be dominated. Not with whips or anything like that, instead the scenes she'd watch over and over involved the starlet being cornered in an alley or biting off more than she could chew at a bar and then being taken against her will. But she knew how people would look at her if they knew that she got hot and bothered by that sort of thing.

She and Josh had just broken up at a party when she spotted the two delinquents in a corner leering at girls. Without a second thought she grabbed an abandoned plastic cup and splashed the remains of it on her shirt giving herself the strong scent of alcohol. Adding a stumble to her step she made the perfect tipsy girl trying to find her coat.

To her satisfaction the boys didn't lead her to the coats but to one of the bedrooms and closed the door. Still acting like she didn't know what was going on she let them get halfway into undressing her before she pretended to gain some awareness and say no. Having already committed themselves they held her down against her weak feigned struggles while one of them got his dick out and stabbed it into her snatch without any preamble.

She hoped that with one of them covering her mouth her moans were being mistaken for cries of protest as they both took turns roughly fucking her and making lewd comments about her enjoyment that were much more accurate than they realized. After they'd both had a chance to cum in and on her she knew she needed to pretend to pass out and give them a chance to escape. Opening her eyes and rubbing her creampied pussy to one last orgasm she wondered how many times she could try this sort of thing before someone got suspicious.


	11. Ann 2

Ann knew the basement needed to be cleaned; a lot of that junk should be donated or just thrown away. It was the kind of job a husband would do but she'd been mentioning it to James since the spring. If she wanted it done she'd just have to do it herself. Fortunately Ron graciously offered to give her a hand, he was always such a considerate man no matter what she needed help with.

This late in the summer the basement was hot and the humidity only kept rising inside its stuffy confines as they shuffled dusty boxes around. Citing the temperate and the fact that it was only the two of them she warned Ron that she was going to loosen up a little. She could have given him a clearer warning but then she wouldn't have enjoyed watching his jaw drop when he next caught sight of her.

Ann hadn't simply loosened her shirt but taken it off completely leaving her naked from the waist up with just a red lacy bra to cover her plump breasts. He was trying not to stare but she could see him sneaking glances as much as he could, making her glad that at least one man was showing some appreciation for the sexy and expensive underwear she'd bought. Even when they finished she didn't immediately put her shirt back on, instead offering to get them some cold treats as a reward for their hard work.

She let Ron munch on his popsicle but rather than bite down on her own she took a long taste with her tongue starting from the bottom and running all the way to the tip. The way she was enjoying her food quickly got his attention which meant it was time to really show him something. Licking it in the most sensual way possible she sealed her lips around the treat, sucking the sugary coating as she lewdly slid it in and out of her mouth, making sure she was collecting the melting juices all the way down to the base.

With a throaty moan she closed her eyes and let a thin droplet cascade down her chin and all the way into her cleavage before continuing her pornographic eating. Ron was clearly too wrapped up in hiding his arousal to realize she was doing this all on purpose and as soon as she was done he thanked her for the snack and made an excuse to leave in haste. Ann hoped she had given him plenty of material to relive in private, maybe soon she might even ask him to return the favor somehow.


	12. Kimcuck

**Notes for the Chapter:**

> This one is a bit different, I was feeling generous and did an on the spot request making it a bit rushed with no revisions.

"So, does this mean you get two votes or can any of us fuck the mascot to sway the vote?"

It wasn't a good start for the squad's senior year as Bonnie questioned her leadership with cutting remarks that implied her new relationship with Ron gave her extra influence over team decisions. Kim was used to it but the summer changed how she responded.

Ron had been amazing in bed, so amazing that she wanted to rub it in other girl's faces. It made her wet imaging how they'd react to his awesome dick so much that she wanted to watch Ron fuck them. And she was doubly curious to see him do it in the one way she couldn't give him herself.

"So we're only doing this for team unity, right Kim?"

Kim had made it seem like this was Bonnie's fault, that she had forced her to do this to keep everything on the squad fair. Now all the cheerleaders had been convinced to shed their tops and get ready. Actual penetration, even oral, was clearly out of line but some harmless tit fucking would be enough to make things equal since Ron would be getting favors from the whole team. She almost bought that excuse herself.

Marcella was first and Kim watched intently as Ron's dick was wrapped between those olive jugs. Her own tiny tits could never hold him like that so she stared excitedly as they were bounced up and down for his pleasure.

Tara was shy so Kim put herself behind the blonde, reaching around and pressing the other girl's boobs together for her, encouraging Ron as she helped her boyfriend fuck the beautiful dick pillows to an explosive finish all over Tara's face.

Last in line was Bonnie and it seemed she had caught onto Kim's game. She held nothing back, happy to show Kim how her huge breasts could please Ron like Kim's never could. Kim countered that in the end Ron was her boyfriend and so she could only hope for a taste. Taking that as a challenge she pinched her nipples and begged Ron to cum in her mouth before making a big show of swallowing it.


	13. Ann 3

Kim's mom was great thought Ron. When she'd heard that he liked Captain Constellation she'd immediately offered him some tapes Kim's dad still had from back before boxed sets were a thing. It was too bad his own dad was so dismissive of sci-fi.

On the little TV in his bedroom he watched several of the classic adventures before reaching a tape that wasn't labeled. Wondering whether it might be one of the lost episodes he put it in but instead of rocket ships he got a close up of Mrs. Possible's face smiling at the camera. It seemed to be a message for Mr. Possible about some business trip and a gift she had waiting.

Ron was confused at first, at least until she stepped back to reveal herself wearing an open lab coat and nothing else. He knew he should press eject but instead he watched as she sat on the edge of a counter with her legs wide for the camera. Drool formed at the corner of his mouth as she spread her pussy lips and began describing in lurid detail how much she was looking forward to being taken and fucked senseless.

It was his dirty little secret that he'd become attracted to Kim's mom. He had started to see her as a sexier, more mature, more easy going version of the girl who he also harbored a crush on. From the difference in the hair style the Ann in the video was probably younger but it was hard to tell, she looked as beautiful today as she did then.

Getting his pants out of the way he started masturbating at the same time that she started doing it for the camera. It was like the Ann on the screen was talking directly to him, telling him how much she wanted him, telling him how much she craved his hands on her body and his dick pumping inside her. Following her words and encouragement he kept going until he couldn't help himself from making a mess that he'd have to clean up as soon as he finished watching the rest of the hot MILF finger fucking herself and talking dirty.

*

When she next saw him Ann asked Ron if he'd enjoyed the tapes. The awkwardness and babbled response confirmed that he'd found the gift she'd slipped in. Pretending to only know about the old sci-fi videos she told him that it was fine and he could keep them as long as he wanted, her husband didn't pay any attention to those things anymore and so she was happy to see a young man like him enjoying them again.


	14. Ron 2

Ron read the message on his phone and then squeezed his eyes for a moment to banish the heaviness from them. Looking across the hotel room he could see the faint outline of Mr. Barkin still snoring in the other bed and so as quietly as possible he got up and snuck out. Outside in the bright carpeted hallway the door to one of the other rooms booked by the cheer squad was ajar and so he wordless slipped inside and shut it behind him.

Immediately Tara was on him, pulling at the drawstring of his pajamas and practically shoving him against the wall before he was even all the way in the room. Softly petting her hair he let the eager blonde set her own pace as she kissed and licked at his hardening shaft before stroking his balls and taking the length into her mouth. Hungrily she sucked on him for several minutes, gagging herself a little bit as she tried to take more than she could handle in her late night excitement for his dick.

Finished with the appetizer she tugged him toward the bed where he wordlessly took over, getting on top of the tantalizingly naked cheerleader and plunging into her without any need for hesitation. Welcoming his firm strokes her pussy warmly embraced his cock while he latched onto a breast and used his tongue to draw tight little circles around one of her nipples. Clutching his head to her chest Tara's breaths became progressively shorter as she whimpered his name and then finally cried out as she came hard around him.

In the other bed Jessica stirred awake and peered over at two lovers with a critical eye before inquiring if Ron had another one in him. Answering that the mascot was always ready to do his duty he slipped under the covers with the other girl and spooned her while his fingers found her wet snatch and went to work. As Tara dosed off in her own bed he put his mouth next to Jessica's ear and quietly asked if she wanted him to fuck her pussy too or if she had her sights set on anal again.


	15. Ann 4

Ann tried not to chuckle at Ron's predicament. Just like her father Kim could sometimes become so engrossed in something that she could overlook the people she should care about the most. Tonight she'd managed to forget that her best friend happened to be a boy, or maybe it was worse and she'd forgotten that Ron was there at all.

Either way when her daughter suddenly changed her mind about what to wear to the Oh Boyz concert she'd unknowingly given Ron an arousing showcase of her developing breasts as she fumbled about in the living room for almost a minute trying to get the new shirt over her head while he remained silently trapped on the couch in front of her. Kim didn't even realize what an uncomfortable problem she'd given him before she bolted out the door to meet with Monique, leaving Ann to see what she could do for the poor man.

Sitting down beside Ron she gently took the pillow he held over his lap and reminded him that she was a doctor and that what he was experiencing was perfectly natural for a man his age. Letting herself be somewhat more erotic then clinical in describing the things it was normal for him to be aroused by when seeing a naked girl ensured that his problem didn't go away and gave her the excuse to offer some help, since in her words it wasn't healthy for him to remain on edge like that.

Once his pants were open she pressed her sweatered bust against his shoulder so that she could reach around and stroke him gently with one hand. The cute little noises he made as she expertly worked on his issue had her fighting the urge to nibble on his ear or whisper dirtier ideas in it. She was sure he knew what this was but for now it seemed like they both wanted to maintain the lie that it was purely medical and totally professional.

Excited by the sound of him whimpering her name she could tell he was close and assured him it was ok to cum. It had been years since she'd been able to feel a virile cock like his twitching in her grasp as he exploded with a satisfied grunt. Ann had to excuse herself quickly, telling Ron she'd get some tissues to help clean up, so that she could get out of sight before hungrily licking his essence from her fingers. She was already looking forward to when she could sample it directly form the source.


	16. Ann 5 and 6

Ann watched Kim and her date walk down the driveway, the boy's hand on her side already shifting lower than what most fathers would find acceptable but as a woman who remembered being that age she could be more lenient in favor of seeing her daughter have a good time on Valentines Day.

Unfortunately Ann's night didn't look like it would turn out as well. The twins had been sent off to a sleepover and she'd changed into her own little black dress with some sparkling new earrings to go along with how she'd dolled up her hair and makeup for the occasion. But all that energy seemed to be wasted after James called to say something had come up at work. The worst part was how nonchalant his short message was, as if he thought this was just any other night to be staying late.

Wondering what she should do next there was a knock at the door; it was Ron checking in to tell her he'd seen the boys off safely to their friend's house. Knowing he had nowhere to be she naturally invited him in, explaining that her own plans had been canceled and she wouldn't mind the company. The way he easily agreed to the idea of spending the evening with her brought all those forbidden feelings she'd been having about him to the forefront.

After sharing some light food and drinks they put the radio on and she chuckled as he showed her what the kids called dancing these days. The evening became even more pleasant as he found ways to compliment her own sway and rhythm. Some time later the music had slowed and they rocked sided to side in a close embrace, his cheek relaxed against her bust and his hands well past where she'd permitted Kim's boyfriend to go earlier.

She wasn't sure if what happened next was because of James's indifference, or the bottle of wine they'd shared, or maybe it was because she no longer wanted to remain on the safe side of the line she'd been afraid to cross. Tilting his head up so she could look into those caring eyes again she made her decision and kissed him. Not a chaste little peck but a lover's kiss in which she boldly pressed her tongue forward and he gladly returned it as the song faded away and all she could hear was their hearts beating together.

The next few minutes felt like she was an observer to her own actions, seeing an elegantly dressed older woman taking a handsome young man by the hand and leading him straight to her wedding bed. Pulling aside clothes haphazardly they rapidly cleared any hints of modesty from each other. It was obvious that they were both too hungry for what was going to happen to waste any more time on just teasing or seduction.

While Ron was lacking a bit in experience Ann had more than enough for both of them and he had no shortage of enthusiasm to learn just where she loved to have her neck nibbled, how to tease her breasts and clit with his fingers until she begged him to enter her and just the right angle and speed to make her cry his name and hook her legs around his waist while she begged him to cum inside her.

His impressive teenage libido kept him bouncing back for round after round. Ann hadn't felt this wanted in years and was driven to guide him into some of the kinkier things she'd only ever thought of suggesting to James. Needless to say as a horny young man he was game for all of it. Finally when she was exhausted and sweaty and oh so sated in every way she bid him goodnight but not before impressing upon him how special he was to her.

Sometime later she felt her husband's weight settle into bed beside her. Despite all that had happened he didn't seem to notice anything was amiss. Ann decided that if he wouldn't pay enough attention to his wife to notice how unexpectedly well sexed she looked that night or even the following morning then it was only fair that she should be able to take advantage of his ignorance to indulge herself with Ron as freely and as often as she wanted to.

**Notes for the Chapter:**

> While I have a conclusion in mind for Ann's story you haven't reached it yet, there should be more coming.


	17. Kimcuck 2

Physical challenges were always a part of the cheerleader's slumber parties and right now it was Liz's turn. As Crystal, Tara and Hope all encouraged her she took a deep breath and made a third attempt, her team spirit pushing hard against her body's own stubborn refusal to go all the way. Finally in spite of her throat's protests she managed to reach the base of Ron's dick long enough for it to count before she pulled away. The subsequent fit of wet coughing did nothing to stop the victorious smile that spread across her face.

Kim joined the others in congratulating her, the squad captain's eyes feasting on the gaggle of cheerleaders all sporting the same mascara stained cheeks after completing the challenge themselves. Doing makeovers first hadn't been her idea but it also hadn't stopped her plan of inviting Ron over since he was a member of the squad and by her argument entitled to attend.

It was a perverse kink of hers to watch other girls experience just how big her boyfriend's dick was and now almost the whole team had studied it thoroughly with their mouths. Bonnie was the last one but she was also the most sure of herself. Indeed she immediately proved her skill by deep throating him in one try, not merely bottoming out but going back for more with the clear intent of blowing him all the way to completion.

Of course Kim wasn't going to let that happen. It wasn't that she didn't enjoy seeing her boyfriend cumming in another girl's mouth but it had to be on her terms. Whispering in Ron's ear he nodded and gripped the back of Bonnie's skull, changing the tempo into a rapid facefuck that left the brown haired beauty gagging frantically. Having reasserted her role as the alpha Kim watched with satisfaction as her man continued using Bonnie's mouth to demonstrate his throat stuffing prowess to the other awestruck girls.

Once he got close he released her and the cheerleaders quickly huddled in front of him like they were taking a group selfie. Coming up from behind him Kim rested her chin on his shoulder as she reached around to rapidly stroke him to completion, aiming his spunk so that it landed on their assembled faces like he was a one man bukkake party. Seeing all of them enjoying and sharing his cum she couldn't wait for Ron to get hard again so he could fuck her alone in the other bedroom while the memory was still fresh.


	18. Joss

Stepping into the busy halls of Middleton High Joss was excited for her first day as a sophomore. She'd convinced her dad to let her move to the big city and live with Kim because it would help her explore her horizons. She hadn't exactly been lying to him however the only horizon she was really interesting in exploring was named Ron Stoppable.

A few years ago she'd been caught up in the hero worship of her cousin Kim but things had changed once she saw Kim's partner in action. Ron was everything: friendly, brave, charming and oh so incredibly handsome. The posters of Kim covering her walls had come down and been replaced with every picture she could get of him instead.

On the lonely country nights she'd lie in bed staring at them and as the years passed and Joss grew older she became more and more focused on one particular train of thought, a train of thought that she had so far satisfied with her fingers and imagination but now planned to sate directly from the source.

Seeing Ron in person for the first time in years she dashed forward and embraced him in a hug, his warm body pressed against hers being everything she'd dreamed it would be. In the time they'd been apart she hadn't gained much in height, never growing past her original petite build, but she was proud of the other ways she'd matured and pressed her nearly b-cup breasts against him in the hopes that he'd notice. Another good morning alerted her to Kim's presence and she broke away to return her cousin's greeting.

As she pleasantly chatted with them she noticed how Kim and Ron's hands wordlessly laced together. Her eyes narrowed at this new development which promised to complicate her plans. But she was a thirsty girl and wasn't going to let something like that stop her. She'd just have to demonstrate to Ron which one of them could be the more generous, more sensual and more kinky lover. Ron was in for a wild ride.


	19. Ann 7

At the last second Ann's hand snapped out and stopped the coffee maker from tipping over onto the floor. Pushing it back against the wall where it wouldn't be jostled by her body again she returned her hand to Ron's shoulder, the energetic young man having never slowed the passionate movement of his hips. Of course she hadn't loosened the hold her legs had around his waist so she was just as guilty.

Indeed after Valentines Day she had initially been the one to continue instigating their sensual encounters. It wasn't that he wasn't interested, he just lacked the confidence and experience to understand that a women like her wanted it too and she wouldn't admonish him for making the first move. But now that he was over those reservations Ann's life was noticeably more exciting.

With his sex drive at its peak he didn't need a special occasion or the right mood to want her in the carnal way. The simple truth was that he was always thinking of her that way and thanks to her encouragement he was now acting on it the second an opportunity presented itself. It had left her horny and deliciously on edge every time that he was around, the anticipation that they could suddenly be going at it like bunnies was a wonderful kind of drug for a woman her age.

This morning all it had taken was for her to start mentioning that Kim was out to deliver the twins for a science field trip and he was immediately lifting her up and sitting her butt down on the counter to ravish her.

Ten minutes later he was thrusting into her with frantic urgency while sucking one of her breasts as she fell through her second dizzying orgasm of the morning. Feeling him nearing his own limit she pressed his face deep into her cleavage to muffle Ron's cry of release and to direct the whole of his shuddering climax into her welcoming body.

In the aftermath her more motherly tone returned and she told him that he'd better get on his way while she took care of hiding the used condom. Ann knew there would be more to it but she didn't want him getting the wrong idea and easing off on these delightful little surprises. In the meantime James might still be clueless but if she showed up to work without a shower and fresh set of clothes first her co-workers would know why she'd been so amazingly chipper lately.


	20. Tweebs

Where the heck was it?! Sure she'd been in a rush after the mission but she was certain that she'd left the last bottle of Dr. Drakken's formula on top of the fridge, safe and sound until she could deliver it to Global Justice who could figure out an antidote. At least the government officials who'd been sprayed with it were all moved to safety so that her arch nemesis couldn't utilize its power of suggestion on them.

Ah ha! She should have known it was the Tweebs. Those little brats thought they could get away but they had another thing coming; not even the world's most dangerous super villains could outrun Kim Possible. The couch certainly wasn't going to slow her down; she regularly vaulted obstacles twice as high and the slippery polished floor wouldn't stop her either. Those boys were going to get a piece of her mind... as soon as she blinked away whatever eye watering smell she'd just stumbled into.

But why was she shouting at them in the first place? Her brothers were just curious; they didn't mean anything by it. Would standing on one foot apologize for raising her voice? It was confusing why she thought that would work. Maybe touching her nose at the same time would clear things up.

Geez, were they still upset with her? Whatever Jim and Tim were talking about it was obvious that they didn't want her to hear what they were saying, it was all hushed whispers and they kept glancing in her direction as if they needed to make sure that she hadn't moved.

Now they were looking at her expectantly so maybe she should say something else? Wait, no; she had a better idea. Her little brothers were curious and at that very moment she remembered what she'd always wanted to do for them. Grabbing the bottom of her shirt she pulled it up to her chin and held it there. Seeing their big smiles made her glad that everyone was happy now.

It occurred to her that she should always keep her tits on display for Jim and Tim, after all she loved it that way, but specifically when Mom and Dad weren't home. In fact once they got upstairs she should probably take off all of her clothes for them. She was going to pose for some photos and they would only get in the way.


	21. Ann 8

Ron thought he was past the age for baths but he was quickly coming around to liking them again. It helped that he was able to stretch out in such a big tub and he definitely enjoyed all the bubbles. But what really sealed the deal were the pair of gorgeous breasts all lathered up and held snuggly around his member by the woman who met his gaze with a wicked smile.

Rolling his eyes back he practically purred as Ann proceeded to use those soft orbs to make rhythmic waves in the water while she moved along his length. When next he looked it was impossible not to see her smug satisfaction and he had little doubt that she'd been planning this exact scenario from the moment that she'd oh so innocently mentioned taking a bath. She had a knack for figuring out what he'd enjoy even before he'd discovered it himself.

However he was pulled from that bliss by an alarming knock at the door. Ron found himself hyperaware of every little sound as Kim, who had apparently dropped by the house for something, casually conversed with her mother from out in the hallway. When she finally left without discovering his presence he let out a long breath which only made Ann chuckle in amusement.

Taking hold of his slightly softened cock she lowered her mouth toward it until at the last second she looked up and asked nonchalantly if he wanted to invite Kim to join them. The question took him by surprise and seeing his blush she pressed on, casually speculating the things he could do with two Possible women at once. Fortunately his stuttered denial was enough to make her stop describing those details and instead tell him to simply close his eyes and relax.

With Ann's lips sealed around him Ron was able to forget about those thoughts but only until she began to alternate between sucking confidently and pulling away to give his dick oddly tentative licks and kisses. It quickly became impossible for him to not imagine Kim was there too, the same lithe body he's only seen in short flashes now bare and sprinkled with bubbles allowing him to freely admire her cute little breasts as she knelt anxiously beside Ann.

Following the sensations he received his mind's eye supplied an image of mother and daughter working together to worship his manhood until all too quickly the experience came to a truly explosive end. Looking down he was both disappointed and relieved to see only Ann who was happily swallowing the remains of that naughty idea she'd managed to sneak into his head.


	22. Appeal

Upon opening the first message Ron had to adjust his legs to avoid any discomfort. The caption "♡↘ Wish you were here ↙♡" floated over Monique's cleavage as the outgoing girl leaned her bikini clad boobs towards the camera. With a nervous swipe the picture was gone only to be replaced by a mirror selfie sent from Tara in which the blonde was wearing a tantalizing set of black lingerie with matching garters. "Just arrived today, want to see it in person?" the accompanying text asked.

Not for the first time Ron wondered why this was happening. He used to be nothing more than Kim Possible's dorky friend and yet in the last few weeks he'd become Middleton's most sought after man. If he and Kim hadn't gotten together a few days before it started he'd have been in (different kind of) heaven right now. The number of pretty girls who smiled at him when he passed, wanted to chat with him at lunch or had sent flirty pictures to his phone was staggering and they were only getting bolder.

Alerted by a ding he cautiously touched the notification icon and immediately regretted it. Wearing a threadbare t-shirt which hung loosely from her tiny frame was a selfie from Kim's younger cousin Joss. To his dismay she was holding a loose fist up to her mouth and pressing her tongue against her cheek in a gesture that she surely shouldn't know at her age. The words "Want to be my daddy?" left no doubt about the meaning causing a bead of sweat to form on his brow.

Swiftly banishing it he moved on to the other texts cluttering his inbox. A smiling Zita Flores claimed that she only wanted to play some video games with him but it didn't escape his eye that the Nintendo Switch that she was holding was also the only thing protecting her modesty.

Meanwhile Vivian Porter had sent him a lengthy message requesting that he take part in a 'scientific inquiry' that sounded suspiciously like it involved her giving him a handjob once he got past all of the big words she was using.

And from an unknown number, which was odd since Wade had given his phone some pretty impressive spy tech upgrades, he'd been sent a picture of a condom nestled between a pair of green tinted breasts that was accompanied only by a set of coordinates and a time.

Closing them all he finally tapped on the message he'd been avoiding. This time there was a video attachment and when he opened it he was bombarded by noisy pop music as Bonnie spun and gyrated around her room while her clothing got left behind. He allowed the luscious cheerleader to get down to her birthday suit but hit stop once he saw her picking up a dildo. That prompted Kim to stop silently snuggling against him and instead nuzzle his chin while telling him to play the rest of it.

Of course that was the strangest part. For some reason his girlfriend didn't seem bothered by him getting messages from other women and it wasn't like he was hiding the contents either. In fact ever since he'd told her about the first one he'd honored her request to view them all together. The thing was... if he didn't know better he'd swear that Kim enjoyed her former best friend and now boyfriend being the target of so much female attention. She was certainly more loud and energetic during the sex that followed these viewing sessions.

**Notes for the Chapter:**

> I wasn't sure what to name this one. If you want to treat it as another cuckquean story you can but my intention wasn't that Kim wants anyone else to have sex with Ron, only that she's smugly satisfied that these woman (many of whom probably teased Ron as well as Kim for being his friend) have changed their tune now that she's dating him and they've stopped to take a serious look.


	23. Ann 9

Hidden behind her dark sunglasses it wasn't hard for Ann to catch men of all ages staring as she strolled down the beach. Her new black bikini drew plenty of attention as the small triangles struggled to keep her captivating figure decent. The reason that they ogled her so openly was probably owing to the lack of any competition; after all she was only accompanied by her teenage son and with his hat down over his face it made him look even younger.

That was one of the most exciting parts about this vacation. Since it was just the two of them everyone at the resort assumed that she must be Ron's mother. It was a liberating misconception that allowed them to openly hold hands and even enjoy one-way kisses without raising suspicion. While she'd been hoping for a sunshine filled getaway with Kim the circumstances of her daughter's cancelation had given Ann the perfect chance to go with him instead, arguing that the ticket was paid for and it would be a shame to waste it.

She certainly wasn't going to let any part of this trip go to waste, not even the task of buying some new swimwear. No one questioned why she would take Ron back to the dressing rooms or noticed when he followed her inside. Fulfilling a fantasy she'd had since college he quickly helped remove her sundress and then prudently covered her mouth before he followed her wish to be taken hard and fast against the thin divider while the sounds of other shoppers echoed around them.

Later in their hotel room there was no more worry about being caught. Suckling at her breast he teasingly called her 'mom' while describing just how tight she felt around him and slowly rolled his hips which sent pleasant tremors through her core. It was perhaps payback for what she'd done in the bathtub but eventually their venture into incestuous role-play melted into a night of passionate love making that lasted until they were both too exhausted to move.

However for Ann the best part was waking up the next day to the warm glow of the early sun and Ron's arms still wrapped around her. Spooned against him she could feel the soft tickle of his breath and the reassuring beat of his heart. As a grown woman she knew that their affair wasn't meant to last but that didn't stop her from committing this moment to memory where she could cherish it forever.

**Notes for the Chapter:**

> One more chapter to go. I'm hopeful of having another (not Ann) entry out in a few days followed by the Ann finale some time next week. If there are other storylines you'd prefer to see continued tell me in the comments.


	24. Anything (Kim)

If there was one thing Kim's parents had taught her it was that you should never make a promise if you don't intend to keep it. It was a lesson she'd taken to heart. Whether it was helping a friend with their homework, getting the yearbook finished for her senior year or saving the world from a peanut-powered doomsday laser Kim Possible had never run from a challenge. Today's mission was no different and despite the unique difficulty involved she hadn't lost her can-do spirit.

It began with a call on the site about a missing actress and when Team Possible arrived at the studio they'd found the director close to a mental breakdown. Apparently the production company had bet everything on this movie and the camera operators, lighting crew and one hundred other actors were all waiting impatiently. If they couldn't shoot this scene today the studio would go bankrupt and everyone would lose their jobs.

Fortunately the girl wasn't in any actual danger. While Kim had been searching the studio for clues Ron went to her home and discovered that 'Tia Tits' was just fine. Unfortunately the winner of 9 adult video awards didn't feel like coming into work today and while seemingly short of breath Ron reported that he was needed at her place for at least a couple more hours. That left the film crew without a female star and Kim was still determined to keep her promise to save the day.

The first blowjob was a little awkward but it didn't take long for the world's most talented teen hero to get the hang of it. Soon she was working like a pro, angling her body so that the camera had a good view of the ropes of cum left crossing her chest and making enthusiastic comments about how good it felt to be plowed by a stranger's dick while she jacked off two more onto her face. She'd never tried anal before but as the saying went in her family anything was possible for a Possible.

With a hundred men to satisfy it took all day for Kim to finish the movie. Captured for millions of future viewers Kim gripped her co-stars butt cheeks and didn't stop until she'd managed to force all 8 inches of his thick member down her novice throat. Meanwhile two more equally endowed men were still synchronized together as they pounded her pussy and ass at the same time making her tiny teen body quiver in unconcealed ecstasy.

Some of the scenarios, like the tit job, were clearly written for a more well-endowed actress but Kim not only saved them but turned what was almost a tired porn staple into a cute and sexy scene of herself using her hands and her boundless enthusiasm to make up for her smaller breasts. By the end everyone was cheering for her as Kim tilted her face up and held out her tongue to receive the last dozen facials, the rest of her body already plastered in semen. With fresh cum dripping from her eyelashes she winked to the camera while licking the final dick clean.

Not forgetting to plug her website she reminded everyone watching that she was "the girl who could do anything" and that was a promise. It was only after she'd cleaned up that a very exhausted looking Ron returned but she had a good feeling that they'd be back at the studio again tomorrow. With a shiver of anticipation Kim wondered if her next mission could have a substitute male co-star too.


	25. Kimcuck 3 and 4

Kim bit her lip and tried not to moan out loud while gazing at the clear outline of Ron's hand under Tara's school sweater. Seeing the way he firmly grasped the cheerleader's ample breast as he pressed her against the locker and suckled at her pulse point made Kim want to cry out just like the other girl was doing. With the blonde too busy clutching at his back to notice Kim didn't feel that self-conscious about dipping her fingers past her waistband to copy what Ron's other hand must be doing beneath Tara's pleated skirt.

It had been immediately obvious that Josh Mankey was a jerk for breaking up with Tara even without the unfortunate timing. Brightening up her Valentines Day was the least that Kim could do for the ever sweet and outgoing girl and right now her own climax was building as she enjoyed watching her boyfriend use his magic hands to make Tara forget all about her dating troubles.

By comparison Zita didn't seem much into dating at all owing to the way that she was always cooped up in her room playing video games. But Kim generously brought her a Valentines Day care package and Zita was certainly grateful to be able to put her hands around Ron's fleshy joystick. He kept his own hands to himself this time, letting the eager Hispanic beauty lick and suck and stroke his member to her heart's content, always slowing down when she sensed him getting close to the edge.

The way she flamboyantly slobbered all over his dick without letting him cum made it seem like this was a game to her, and if so the score must have been the number of times Kim lost control and shuddered in the seat next to Zita's computer. Kim loved how enthralled another girl could become just from touching her boyfriend's penis, though for Ron's sake it was good that Zita eventually relented and directed his overdue load into her waiting mouth.

Of course Bonnie had always bounced between boyfriends which resulted in the happy coincidence that she had no one on Valentines Day. Kim had been talking with Ron about it for a while now, her desire to see him doing more, how she really was ok with him enjoying other woman and that she wanted to watch him going all the way with a girl. Despite or maybe perhaps because of their rivalry Bonnie seemed like the perfect choice for them to agree on. She was unquestionably hot, very willing and unlikely to have any sticky emotional attachments to deal with later on.

Inviting the smug brunette into her bed was easy but not letting her claim the upper hand was harder. For the first time Kim found herself joining in and treating Ron to the sight of her and Bonnie's lips fighting over his dick. Being naked and practically making out with a woman wouldn't normally do anything for her but the thought that this was getting Ron extra hard so that he could finally fuck another girl certainly did the trick.

When Ron did consummate the act he blew past all of Kim's expectations. She'd told him in advance that she didn't want to see him just fuck her rival; she wanted to see him absolutely wreck her and he didn't disappoint. While pounding Bonnie's wet pussy he also mercilessly played on her clit leaving no chance for the poor girl to rest between orgasms. It did take Kim by surprise when he wrapped a hand around Bonnie's throat but the slutty girl seemed to love it, calling him daddy and begging him to choke her harder and stuff her fuck hole with his amazing cock.

Afterwards Kim couldn't wait for Ron to start round two and waved her butt at him invitingly. Doggy style was rarely their thing but this time it allowed her to look down at Bonnie's cum decorated face, the nubile girl's eyes open but unfocused as her mind must have taken a break after too many neuron zapping climaxes. Feeling as good as she did while he made love to her Kim didn't stifle the obscene urge to lean down and lick some of her man's seed off his most recent conquest.

Left exhausted but utterly euphoric from the whole experience Kim nestled herself in Ron's gentle arms. Charmingly in tune with her sense of romance he whispered in her ear, telling her how tightly Tara's pussy had clamped down on his fingers, of how enthusiastic Zita's tongue had felt tracing his cock and most importantly endorsing her thoughts that tonight he, her boyfriend, had completely ruined Bonnie for any other man. It was the best Valentines Day ever.

**Notes for the Chapter:**

> I hadn't planned on doing this chapter so soon but I realized at the last moment that I hadn't written something for Valentines Day. So I pushed myself to produce something appropriate utilizing some of the ideas I'd written down along with some new stuff. I think the next entry in this series will probably be from Ron's perspective.


	26. Tweebs 2

Fluffing the pillows one last time ought to do it. Wait, did she tell Jim and Tim that she was cleaning their room or would this be a surprise, she couldn't quite remember. Well either way her brothers wouldn't be disappointed after the hours of work she'd put into this. Not like the disappointing news from Global Justice. How could the bottle of Dr. Drakken's mind control formula that she'd kept safe turn out to be ordinary tap water!?

Well there was no point in worrying about that now with the sound of familiar footsteps approaching. This was it! She needed to get rid of her blouse fast so that she could greet her brothers the way she liked to: sitting on her knees, hands behind her back, smiling wide and arching her chest out proudly. Now which made her feel better? The way they gaped in awe at the spotless room or how quickly their eyes snapped to her when she gave her perky breasts a small wiggle.

Maybe she could make them even happier if she did their homework too. But wait, no, that was a dumb idea. They were so much smarter than her. She was a dumb girl and would mess it all up. But if she did do their homework then they could play more video games, wouldn't that be better? Nah, it was still a bad idea. Or was it? It seemed really hard to make up her mind.

But why fuss over that when she'd just thought of an even better way to show her brothers how much she cared. Tim was thankfully trusting when she asked to open his fly and even let her stroke his dick before she began to lick it to hardness. She might have taken this a little fast for her first blowjob but she just really wanted to suck him off right now and his warm spongy member felt so right in her mouth. By his moans Tim seemed to be agreeing too, she was the best big sister ever!

Wow, she wasn't expecting that to happen so soon. It was so bitter and salty, it oozed between her teeth and gums and... it was the best thing she'd ever tasted. She swallowed Tim's seed as quickly as possible and then pressed forward to lick off any that might be left over. She knew there was more like it to be had only a few feet away and thankfully Jim didn't refuse her wish to suck him off too.

It was great to discover something that all three of them could enjoy doing together as siblings, it made her feel so excited that she just had to give herself a squeeze and brush over her hardened nipples. From now on she'd greet her brothers like this every day: on her knees, tits out and eager to give blowjobs to the both of them. And it would be 'totally badical' if she got an early start right now by getting Jim to spray his cum all over her face!

**Notes for the Chapter:**

> Let me know if this storyline should continue


	27. Ann 10

Ann took another sip from her coffee just as a long moan echoed from the vent near the stove followed by a muffled cry that sounded like 'Ron'. Tomorrow she'd need to find a way to tell her daughter about the attic bedroom's unfortunate acoustics. Hopefully Kim wouldn't look as mortified as she had while receiving the 'cool mom' talk - how she could have Ron up there with the door closed as long as her father and brothers were out of the house and she was being 'safe' in whatever they were doing together.

It was still a palpable relief that Kim had finally realized that her perfect man was right there all along. Ann almost felt sorry for that Josh boy since after seeing how free he was with his hands she was certain that Kim must have been letting him do a lot more than just kiss. Right now Ron would be making him and the other boys her age seem particularly inept by comparison.

After Kim had let slip that her feelings about Ron were becoming more than platonic it had been Ann's turn to make a choice. Her affair with Ron was still going strong but in the long term he was the right one for Kimmie and she wanted her daughter to be happy more than she wanted to continue fooling around behind her husband's back.

Ending their relationship and convincing Ron to pursue Kim were largely one and the same. She knew that he had feelings for his best friend, feelings he'd buried because he thought they might ruin something dear between them. But Ron trusted Ann and so he listened with an open mind when she explained that Kim was stuck in precisely the same predicament concerning him.

In the end she left him with a simple question. Did he want to keep having clandestine sex with a willing and voluptuous older woman who was willing to make his dirtiest fantasies a reality? Or did he want to spend his life with Kim? Being with her, holding her close, sharing their ups and downs and finding a future together. Plus he'd finally have that tight cheerleader ass he'd been ogling for the last three and half years, something that Ann pointed out that he'd only been getting away with because father and daughter were equally oblivious to his drooling gaze.

Later when Ron came downstairs Ann was still waiting for him. There wasn't much point in asking if Kim had enjoyed it so instead Ann licked her thumb and wordlessly rubbed away the traces of lipstick on his chin. It wouldn't do for his parents to become suspicious. There was a part of her that wanted to make a joke about whether he'd be up for a round with her too but she'd chosen to leave that behind and not revisit it except as a happy memory.

Instead Ann wished him a good night and let him give her a loving kiss on the cheek before sneaking out the kitchen door, the same side entrance that she had so often looked forward to hearing him enter from.

**Notes for the Chapter:**

> If I'd kept second guessing whether this was a good enough ending I'd probably never get around to writing anything else... so here it and hopefully you enjoyed the journey. I'll still be updating some of the others and maybe starting a new one or two when time permits – I have a request for a particularly saucy Ron/Bonnie story but I'm also looking for thoughts about the mood/setting for a more romantic Kim/Ron one (before or after they're officially a couple?)


	28. Alternatives

Ron's boots echo on the metal floor as he strides into the command center where giant displays showed his master plan unfolding. Coming up behind the figure wearing a familiar green and black garment he casually flicks the new clasp that sends it puddling to her feet. The henchmen working the computers wisely keep their attention forward since the sight of Shego's glistening nude body is reserved for his eyes only. Reaching around from both sides he claims her bountiful breasts with a dominant squeeze, pressing his fingers into the subservient flesh and making his sultry green enforcer purr as she melts back into him while they watch the whole world falling to the might of Zorpox the Conqueror.

_Crack..._

Ron can feel the mystical energy rising through him as he floats a few inches above the woven mat. As the Yamanouchi School's latest sensei it's important that he be balanced, a difficult task when his meditation is abruptly challenged by Yori's lips on his member. Keeping his eyes closed he tries to keep himself detached from the physical world for a while longer, at least until the physical world takes him to the bottom of the warmest, tightest throat he knows. Landing with a thud he can't tell where she's escaped to, as befits a ninja, but he's gotten the message. If he wants his wife to stop being so naughty he'll have to put another baby in her.

_Pop..._

Ron lets fly another stack of hundred dollar bills to the cheer of his posse and the students following in his wake. Exiting school as he does every day he coolly steps into his gold clad stretch limo with the plate that reads NACO99M. Champagne and caviar are already flowing freely as he puts an arm around his number one babe Bonnie and gives a nod toward his crotch. Happily she sheds her tube top and soon enough those sexy breasts accented with the diamond nipple studs he bought are wrapped around his dick. Groaning in pleasure he wonders what expensive trinket he can buy today to go with the pearl necklace he's going to give her.

_Buzz..._

Ron allows his lips stray away from Liz's long enough that Marcella can use her teeth to lower another delectable cherry into his mouth. Jessica is still riding him wildly, her hands braced against his chest as her eyes roll and she seizes in ecstasy. After that it doesn't take long for her to be dragged off, Hope and Crystal already using their tongues to fight over his dick in the hopes that they'll be the one who gets to be fucked in the ass today. Taking a moment to reflect on the catastrophe which left the world inhabited almost exclusively by horny woman he mumbles to himself how good it is to be the King of Middleton.

_Crunch..._

Ron can't believe that it's his cousin's wedding and Monique is still slipping under the table cloth at the first opportunity. He needs to take her to the coat room or something, soon, so that he can give his sweet but hopelessly exhibitionist lover a proper semi-public fucking. Hopefully if he can exhaust her with an enjoyable but risky pussy pounding early on she won't be able to get them into any real trouble later.

_Sizzle..._

Ron tries again but the ropes wouldn't budge. Leaning back against the leather-clad headboard he shivers thinking about what kinky delights Mistresses Connie and Lonnie have in store for him tonight.

_Creak..._

Ron cries Tara's name and unleashes his load the only way his soul mate will permit it: spread messily across her eager face.

_Snap..._

Ron knows it's so wrong, but Joss's hands makes it feel so right.

_Boom!_

Falling to his knees Ron clutches his head as soon as the malfunctioning dimensional plotting machine has finished destroying itself. Kim is already at his side, holding his shoulder and asking him if everything is alright. Strange, impossible memories hurl around like a blizzard inside his brain but when he looks up those thoughts settle at the sight of the amazing woman he's with. Feeling a smile spread across his face he takes Kim's neck and pulls his girlfriend down for a gentle kiss while assuring her, to Kim's slight confusion over his wording, that everything is exactly the way it's supposed to be.


	29. Kimcuck 5

Pom-poms gave way to pussy as all seven cheerleaders rushed to drape themselves over the bench, flipping up their skirts and forming a line of bare butts all begging to be banged. Focusing on the girl beside him Ron observed Zita's dry-mouthed fascination with the raunchy sex scene playing on her computer screen. He wasn't sure how they'd gone from browsing reaction videos to watching her library of bookmarked porn but for the moment he was just trying to avoid making it awkward.

For an attached guy the notion of spending hours alone in another girl's bedroom would be risky even without the pornographic content. But Kim wasn't an ordinary girlfriend by any measure. Ever since Valentine's Day she'd been enjoying a new confidence with her fetish, arranging an encore of his performance with Bonnie in the school's locker room so that the entire cheer squad could see it. Once word got around about him fucking the brunette senseless Kim had no shortage of willing volunteers as she began asking him to bed his female classmates one by one while she watched and gave kinky suggestions before ravaging him afterwards.

Now as the screen showed another outlandish scenario about a scarlet haired MILF seducing her teenage daughter's boyfriend Zita began to talk about her own sex life, or the lack there of. Of course she wasn't complaining and pointed out that masturbating made more sense compared to the work and drama of maintaining a guy. The idea that losing her hymen was a special right of passage seemed silly to her too but she did have one reservation: if she eventually met a guy whom she fancied emotionally, maybe in college, she might spoil it by appearing like a total newb in bed.

And that was how Zita popped the question which left him fumbling for an answer. Kim always picked the girls she wanted to see him fuck and that also meant she would be there with them. But today Kim was practically a prisoner in the library with her history project due next week. Zita's request seemed time sensitive and she'd obviously been working herself up to it; it worried him how she'd handle any rejection or delay. Faced with the daunting peril of the female mind Ron used his lifeline to call Kim whose answer was surprising simple: ask if she was ok with recording it and if she was go ahead and rock Zita's world.

Now Ron would be lying if he said that he didn't enjoy Kim's kink a lot. The fact that his girlfriend was helping him score with tons of other hot chicks was a teenage boy's wet dream. But today he endeavored to keep his libido in check. This was Zita's first time going all the way and he wanted it to be especially good for her. Burying his nose in her curls he licked her to orgasm until she was yanking his hair and screaming for him to stuff something bigger than fingers inside her.

Fortunately everything went as smoothly as possible and before he knew it she wanted to assume her familiar position as player one, flipping him over and lining up his dick with her slick folds before sinking down with a blissful sigh. Letting her ride him with vigor Ron was content to help Zita try whatever position she liked, exchanging rubbers as they went a second and then a third round together. All in all he was pleased to leave her with an impression that while sex wasn't entirely like in her videos it was just as if not more enjoyable than it looked.

However for Ron there were still lingering doubts about how this affected his relationship with Kim. Was she turned on by cuckqueaning so much that she wanted him sleeping with other girls even when she wasn't around, or had she given the ok because she thought he was asking for himself and she felt pressured to say yes because he'd always said yes to her? They'd hardly had any time to talk today with her project still incomplete and the uncertainty was driving him crazy. 

His answer came when Tara awkwardly approached him in the hall after last bell. She seemed anxious and he was waiting for her to say whatever it was on her mind when she instead took a nervous look around and then pulled down the neck of her shirt far enough to expose a blue note scrawled on top of her breast:

> Give Tara some Ronshine, band room should be empty  
She's taking the pill so NO condom + finish inside  
P.S. Remember to take plenty of pics ❤❤❤ Kim

**Notes for the Chapter:**

> This chapter is from Ron's perspective so we didn't get to see a scene of Tara approaching Kim in the library and fumbling for the right words to ask if she could be on the list of girls Kim is going to get Ron to have sex with. Kim's mostly concentrating on her essay but grasps the gist of it and spends a moment unsuccessfully looking for a blank page to write on, then without missing a beat she lightly grabs Tara's shirt and pulls her down to record the note right on her breast, cheerfully saying to just go and show him that and then nonchalantly going back to her project. The note itself is a tribute/homage to the NSFW artist Hagfish who has created some classic Kim cuckquean artwork including a recent Kim/Ron/Ann comic strip.


End file.
